Sort by
Relevancy

Free Stories

46%
Important And Interesting Observations About Online Porn
What is your opinion about watching best porn video online? Is it a bad habit? Is watching porn good for a relationship? Pornography has become a common part of the private lives of many individuals and partners. Nobody can disagree with this fact. Online porn can be used as a great tool by couples ... Read full Story
CollectionofBestPorn 2017-04-01 2,739 Big Tits hardcore porn anal porn
90%
Sissy story and 1st meet humiliation
I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before tal... Read full Story
shemale lover 2014-11-19 25,212 ass Fetish domination cd sissy
93%
Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
shemale lover 2015-05-01 14,873 first time ass Cumshot suck cd sissy make up
100%
Riding the Lakefront Part 2
The event that actually changed my life began when I needed to piss about 6:30pm while on my bikeride. Tightfitting bike shorts were worn because of the padding in the ass area. But had I worn a pair of shorts with a zipper, none of this would have happened. Had I not worn a zippered tight biker shi... Read full Story
shemale lover 2012-04-11 2,073 hardcore pissing
80%
Outdoor Tranny Sluts Lust
I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... Read full Story
Tracy Bel 2023-02-14 5,227 Crossdresser Outdoor Fetish Homemade cum in mouth shemale + shemale
100%
Cross-Dresser Fucked by Hot Sissy
Today I was feeling particularly horny and decided it was time to get some action again...! I jumped online and setup an online account with adult friend finder! With my online account setup under my assumed identity I tentatively chose some revealing photos to upload... It didn't take more tha... Read full Story
shemale lover 2013-01-22 4,567 hardcore sucking ass fucking doggy style deep throat
50%
SISSY AWAKENING
- Trou de gloire du sex-shop - "Hey bébé, quand est-ce que tu rentres à la maison?" le message texte bourdonnait doucement. Sortant discrètement le téléphone de ma poche, je tape "Même heure que d'habitude, juste après 5 heures, pourquoi... quoi de neuf ?" C'est mon amante Sarah, ma meilleu... Read full Story
Femboy 2021 2023-02-17 978 Stockings Crossdresser Outdoor Fetish Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys cum in mouth
91%
My first big cock
So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective. I tried an online dating site ... Read full Story
Cbosh40s 2015-03-31 10,101 anal Crossdresser hardcore Mature sissy
50%
LE GRAND MAGASIN SISSY ⚧️ ⚧️
« Vas-y, embrasse-le, Christina. Tu sais que tu le veux ! Je suis Christina, et c'est ma petite amie, Sandy, qui me dit d'embrasser la bite dure de "Jamie" alors qu'elle dépasse de sa culotte en satin noir baissée. Son sexe est dur, mais doux au toucher, et mon cœur bat la chamade alors que je le... Read full Story
Femboy 2021 2023-03-28 921 Stockings Lingerie Sex Toys humiliation sissification cum in mouth poule mouillé féminisation Sissy
56%
Teen Sissy getting ready to give herself to daddy for xmas
Hey Im Rosie and im 22 from the UK im a aspiring sissy slut and i have been getting myself getting my whole body smooth ready for my daddy ready for my daddy for xmas / new years i have found out he has been watching ts / ladyboy porn for a while now and i have allays wanted to become his sissy slut... Read full Story
English Rose 2016-12-23 6,174 tranny ts cd sissy daddy xmas
83%
The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
badbadboi667 2021-01-04 4,676 Crossdresser Amateur Group Sex Outdoor Bareback Creampie Blowjob Big Cock gangbang domination Homemade Ass to Mouth cum in mouth
92%
The first sex! A dream for a little sissy slut!
We decided to meet at your place, I enter quickly and immediately go into the bathroom to get ready for our spicy evening. I'm already shaved and wearing stockings, leopard print panties matching bra. In the rush I'm doing makeup, I get dressed in little black dress, barely covering my bum! I put a ... Read full Story
shemale lover 2013-08-09 5,370 Stockings hardcore Cumshot Lingerie domination spanking
89%
Becoming a Sissy Slave
He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You ... Read full Story
shemale lover 2012-03-05 16,618 hardcore deepthroating cum swallowing facefucking
80%
Owned sissy girl
I met the mature dominant couple that I now call Mummy & Daddy on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for... Read full Story
Andrina62 2015-09-23 28,652 anal ass rimming cd sissy
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 3,807 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
87%
A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
shemale lover 2012-05-27 10,381 Stockings anal sex Fetish Interracial sissy
70%
First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
shemale lover 2012-10-27 16,561 first time Fetish Big Cock domination sissy
70%
Becoming a Sissy - My aunt my Mistress
For more than 6 months i’ve got this fetish, whenever my mom is out i crossdress with her clothes. It all started with porn, and slowly i got courage and from a pair of panties i ended up full crossdressed, with the make up made. Everything changed on this day, when i decided to crossdress even ... Read full Story
sissy emma 2017-10-05 73,680 Stockings Crossdresser domination cd sissy high heels
100%
My experience with sissy hypno
So, I have decided to make my experience with sissy hypno known so it can act as a testimonial. Sissy hypno works! Interpret that however you want. When I was younger, naive, I was a man, I worked out, I had no interest or desire in cross dressing. I looked at porn occasionally and I was clickin... Read full Story
Jenna_NB 2023-01-31 4,343 jerking sissyboy sissy slut hypnosis sissy crossdresser femboys non binary
100%
Becoming Sissy
I remember my first true and sober gay sexual encounter. The guy from the party that was my first BJ and first penetration was one of the closest friends of the group. He bought a house up north and 3 of the girls and me went to his house to help paint and work on some things. This was about a mo... Read full Story
xspeeny 2023-04-28 7,318 anal Amateur Bareback Blowjob Big Cock sissy cum in mouth
100%
The reason why I show me on porn sites
The reason why I show me on porn sites is I am an exhibitionist. I feel like I've become a porn star when people watch my videos. Also, I sometimes masturbate in front of hundreds of viewers on live webcam sites. Maybe, I'm waiting someone who knows me find me on porn sites. The someone ... Read full Story
cdmisato 2024-04-02 1,559 Crossdresser Amateur sissy
66%
A Sissy's Wish List
Boys, boys, boys. First off, let me tell you that I have a butt plug shoved so deep in my little tranny pussy right now. That might help to explain how depraved I might sound. I really need some cock in my ass right now! I am sitting here stroking my tiny little tranny clit right now thinking of how... Read full Story
shemale lover 2012-06-19 4,195 transformation submissive sissy
72%
Black Man's White Sissy
I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my ... Read full Story
shemale lover 2012-07-03 9,162 Cumshot oral sex sissy
66%
Elizabeth: Beginnings of a Sissy
I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her... Read full Story
shemale lover 2012-04-02 4,422 first time Fetish Blowjob facial Sex Toys sissy
84%
Lesser of Two Evils
My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... Read full Story
shemale lover 2013-03-27 22,439 hardcore Cumshot sucking ass fucking Guy Fucks Shemale
91%
Birth of a New Sissy Part 1 Encounter
I met Jeff one day at the nearby tennis courts. I could never have imagined what the result of that meeting would be. I suppose I should tell you a bit about me. I'm a happily married 34 year old. About average in most respects. A little spare tire trying to form around the middle but in decent ... Read full Story
shemale lover 2011-11-17 5,106 cum Sex Toys crossdressing
100%
HELPLESS TO MY CRAVING FOR BLACK COCK
This is a totally true account of my addiction to meth and its hand in turning me into the he[pless sissy I've become to my weakness for BBC. My name as a regular male is Richie Budd. But by reading this you'll soon realize that nothing is normal. Not only was I Richard Budd. I spent an equal, if ... Read full Story
Tvtrinity 2021-04-07 9,451 Crossdresser Amateur Group Sex gangbang Interracial transgender sissy bbc Black Owned owned white boy pimped force feminised BNWO
50%
Aunt Susie's Training Part 5
Aunt Susie and I woke up around 1030AM and Aunt Susie said we need to get ready for a surprise appointment in the city. We put on our make up, I pulled a ponytail again and we got dressed in jeans and heels and matching white button down shirts which we left untucked. We drove first to Aunt Susi... Read full Story
BITCHGURLvr 2024-05-09 81 cock sissy Cigarettes
100%
HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
CDDIXIE4U 2019-01-08 13,196 Teen (18+) Crossdresser Amateur Cumshot Masturbation Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Homemade Compilation Vintage cum in mouth
62%
Crossdressed Lana - Hannover, Germany
Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... Read full Story
Crossdressed Lana 2020-02-06 3,973 Stockings Crossdresser Group Sex Outdoor Bareback Fetish Blowjob gangbang Lingerie domination Latex Sex Toys double anal
59%
NORTH HOLLYWOOD GAY BATHHOUSE
Hi so the first time i went to a bathhouse was when i was 18 , i was dating a 44yr old dominate top tranny (Tina) who had the biggest uncut latino thick cock, her cock was the one that made me not only give up on girls but she turned my body and mind into a complete bottom sissy , my butt became her... Read full Story
daddyssissyla 2016-02-22 12,715 anal submissive sissy bbc doggy styду
50%
How I Learned To Love Drag Part 10
As I stood on the first tee of the Royal Vancouver Golf Club, I must admit that Lotus Land sure had a lot going for it. On one side of me was a breathtaking view of the Pacific Ocean. In front of me was one of North America's finest golf courses. And in the distance was the snow-capped peak of majes... Read full Story
shemale lover 2011-12-31 2,209 hardcore erotic encounters fantastic
58%
My real story
I couldn't believe it. Here I was in bed with an older man – and one that I most wanted as he lay there sated by my ministrations to him. It had all started two weeks earlier when I had posted an ad on Craigslist. Up until this particular posting I had always been pretty bland..."Willi... Read full Story
shemale lover 2012-06-10 6,052 hardcore Cumshot bdsm oral sex
71%
Creating Alyson
"Is it an acid?" Diana answered hesitantly. My snigger from the back of the room told her it wasn't. I knew people thought me arrogant, and a know-it-all, but as usual I couldn't resist. All year during the chemistry classes for the science course she was following, Diana had strug... Read full Story
shemale lover 2013-01-11 4,925 Crossdresser hardcore sucking Blowjob oral sex
100%
Such a whore
I finnaly made this happen a few days ago ! i have been crossdressing for as long as i can remember.I still remember when i snathed a pair of my cousins panties when i was young i dont know theres is just something about womens clothes that just intrigies me . Any way growing up i always masterbate... Read full Story
shemale lover 2013-05-31 5,258 Stockings hardcore Cumshot suck sucking jerking doggy style cd
90%
Riverbank Tranny Fucktoy
Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... Read full Story
shemale lover 2014-12-03 4,508 tranny hardcore suck Big Cock cum ass fucking deep throat
84%
Becoming a Shemale's Bitch
I just got into town and spent the whole day moving in and cleaning my new apartment. I didn't have much furniture but the place needed a lot of cleaning. I saw their was a bar a few blocks away from my apartment and decided to go out for something to eat. It was around five o'clock when I walk... Read full Story
metamafia 2012-12-21 118,050 hardcore Cumshot sucking bdsm domination
100%
Dressing and driving
A little about me, I'm married, and wife doesn't have a clue I like to dress up. I would love to have her know and accept it, but I don't think she would. I do cam and love to get instructions from people that are watching on cam. Am I a sub? I think I am. I like to drive dressed. When I take a driv... Read full Story
SandyCrossdresser 2018-11-26 5,458 Amateur Outdoor crossdressing driving Reast area
100%
Sklavin Pia
Ich bin Ich bin die Pia eine sehr devote 2 LochSchlampe und eine (nahezu) tabulose, versaute, hemmungslose und spermageile Schwanzhure, immer auf der Suche nach Sperma und Schwänzen werde am liebsten in frivolem und nuttigen Schlampendress vorgeführt, mag spritzige und spermareiche Spiele mit mögli... Read full Story
Piatvhure 2022-10-31 2,131 Crossdresser Amateur Outdoor domination
75%
Tranny whore Samara Rosetti at a Trucker's jo
Last night I got a call from a client. He told me to meet him at a small bar close to Olga Street in Stuttgart. He ordered me to dress as follows: Short black leather mini skirt slit up the side, button down red silk blouse unbuttoned 3 buttons, 16cm spiked heels boots, fishnet body stocking, no br... Read full Story
shemale lover 2011-09-25 6,877 anal shemales hardcore
100%
The Greatest Lie Part 9
Two hours after saying goodbye to Rick and Randy, Tran and I left Minneapolis and boarded a plane to LA. I fell asleep at take off, and woke as the plane began its descent. Tran was staring out the window at the city’s lights spread in an endless shimmering galaxy below. "Wow, I love LA a... Read full Story
shemale lover 2012-01-19 3,611 hardcore erotic encounters fantastic
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,191 Crossdresser hardcore ass fucking cd
66%
Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
Go Balls Deep or Go Home 2018-08-06 30,948 Crossdresser Outdoor Bareback Blowjob Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
50%
A Shock at the Adult Theatre
I am very often thursdays in the adult theatre, because stylde crossdresser have free entrance at this day. I used to go there by public transportations, because I have no car. In the rear area of the shop we are able to change our clothes and to style up and storing our bags in a locker. About a... Read full Story
SilkeTrav 2020-01-20 7,702 Crossdresser Amateur Outdoor Masturbation Lingerie Homemade
100%
Karen, My School Teacher Part 5
The Bus Station By FoxyHosed I looked around, but no one was there. It was dark and pretty cold night outside. I felt the air blowing around and up my pantyhose encased legs and ass. Mmmm nice. I started walking to the bus stop a few blocks further down from the school. I felt very attractive g... Read full Story
FoxyHosed 2021-03-15 6,767 Crossdresser Cumshot Outdoor Masturbation Fetish Blowjob pantyhose legs pantyhose cd
100%
Trans sucht Daddy
( Anonymität Diskretion ) Schreibe eher über mich Geschichte meine Sex Lebenslauf !!! kommt Später Da ich ja aus Erfahrung weiß da viele Herren auf Anonymität angewiesen sind und wert darauf legen dürfen mich sehr gerne was mir auch sehr Gefällt mit Maske im Hotelzimmer + Ferienwohnung besuche... Read full Story
Tranny ( Für den ) Herrn 2022-08-24 1,750 tranny crossdressing transgender tv crosssdresser cd solo daddy sissy crossdresser daddy fucks sissy grandpa DWT TV Transe BI
100%
Shemale Porn
Nowadays, I masturbate exclusively to shemale porn. Like most guys, I started out reading, then watching, straight pornography. Sure, there was the titillation of happening across a cross-dressing tale in the glossy flesh mags, but they were for a ‘straight’ readership, and didn’t quite scratch that... Read full Story
Daddybear71 2023-05-24 7,300 Crossdresser Amateur Masturbation
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 1,192 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
50%
Lust and Love with Leona
This is a work of fiction. * The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn't pull in a bar. But I found that I could not s... Read full Story
shemale lover 2011-10-07 4,283 hardcore celebrities oral extreme
95%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 30,437 strapon porn
100%
Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
shemale lover 2012-05-21 7,077 first time hardcore anal sex Cumshot oral sex crossdressing
87%
Both Sides Of The Coin
Jessica and I were back at the scene of the crime, so to speak. Her work friend, Mike, hosted a costume party every year on the Saturday night 8 days before the Super Bowl, "Because there's never anything else going on that weekend." Last year, that tagline on the invite offered suffic... Read full Story
shemale lover 2013-01-28 5,279 Cumshot Outdoor sucking Blowjob deeptroat
100%
An Orgasmic Uber Ride
"Chris?" the Uber driver asked me after driving up and rolling down his window. "Yes," I replied and then I got into the passenger seat next to him. I usually ride upfront in Uber rides because I get car sick easily in the back. After fastening my seat belt we were off. The guy was older, maybe ... Read full Story
Chrissy Tunnell 2022-02-18 3,186 Crossdresser Amateur Outdoor Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
50%
The Greatest Lie Part 18
They say that prostitution is the oldest profession. I disagree. Some guy must have been a professional hunter to have gotten together the spare change to pay for that first commercial fuck. It's like that chicken and egg conundrum. Eggs definitely came first. Just as mutation precedes evolution, th... Read full Story
shemale lover 2012-01-20 3,967 taboo hardcore femdom
83%
Tgirl Shemale porn cinema slut
As you know I'm very much a normal living sort of TGirl, cooking, shopping, cleaning, just day to day stuff like everyone else...I haven't started baking cakes for the local Women's Institute or joined a knitting circle yet, but I'm sure you get the general idea!! Sometimes, however, I get the ur... Read full Story
shemale lover 2012-05-07 4,503 shemale oral sex bikini heels
100%
What i'd like to experience
So everynight I come on here and beat my cock watching anything that attracts my attention. I started off with the hardcore porn and found most of the hot chicks on here just simply boring. too much acting and advertising just wont give me that hard cock to beat. so I fell in love with the mature, c... Read full Story
shemale lover 2012-10-29 2,601 double penetration cum licking